This research explores the effect of orientation advice (OA), which is an instrument aimed at supporting pupils during their first transition from middle to high school. We investigate whether being 'ambitious' (i.e. rejecting OA and choosing a more challenging track) influences grade 9 retention probability. Data from 28 schools from Piacenza (Italy) are combined with those of the Italian National Evaluation Committee for Education (INVALSI). Employing the propensity score matching method, we find that being 'ambitious' increases the probability of grade 9 retention by 10-15%. Moreover, making an ambitious choice is riskier for males, non-Italian and socioeconomically advantaged students.